> I think this could work if you did this at the time your company launched, but the moment you have employees who have Apple IDs tied to their work email that aren't from the Business Essentials system you are stuck in an impossible-to-mange place.

I had the same thing happen but with Microsoft. A friend and I had started a small consulting business and were using Google Workspace, but I needed a Microsoft account to interact with a client. I made one with my business email. None of us knew any better, but I couldn’t connect with our client’s Microsoft setup because it was a personal account. So I went to set up a business account. It was a whole fiasco and the only way I could really fix it was create an alias and use that for Microsoft.